As the Iran conflict continues, Professor Siegel expects short-term pain, but isn’t concerned with the long-run. There’s been a lot written about AI destroying software, and while the concerns have merit, a lengthy Goldman Sachs research report highlights winners and losers. As tax-time approaches, we dig into some tax planning items, explaining strategies high-net-worth investors are using to reduce capital gains taxes and the benefits of the new senior standard deduction. I also share a useful reminder on protecting your data from your phone’s apps and what financial information to share with your heirs, as well as a local real estate update in our Boston Corner.
This Week’s Takeaways:
- High-net-worth investors are increasingly using strategies like borrowing against appreciated assets, derivatives-based hedging, and systematic tax-loss harvesting to access liquidity, manage risk, and rebalance portfolios while deferring capital gains, improving after-tax outcomes and giving them greater control over when taxes are realized.
- There is a standard deduction increase for seniors through 2028, reducing taxable income and giving retirees more flexibility to manage taxes on withdrawals and investment income, which provides planning opportunities.
- AI compresses value in commoditized software but expands the overall opportunity set, shifting economic power toward platforms, data-rich ecosystems, and companies embedded in core workflows rather than eliminating the need for software altogether.
- Sharing key details of your estate plan—if not exact numbers—helps heirs avoid confusion, delays, and costly mistakes when it matters most.
- Investors should be cautious in the short-run because of higher oil and the Iran conflict, but the larger outlook is still positive as the economy is still growing, labor has not cracked, inflation was better than feared, and the secular AI story remains intact according to one market watcher.
- Popular apps are secretly harvesting user data and selling it to advertisers. Users should regularly review app permissions through iOS Privacy & Security settings or Android’s app-specific permission menus to restrict data access and delete problematic apps.
- Our Boston Corner has a local real estate update and a list of the most affordable top towns in Greater Boston right now.
Slashing Tax Bills for Rich Investors Is a $1 Trillion Business by Bloomberg
High-net-worth investors are increasingly using advanced strategies to reduce their capital gains. Common approaches include borrowing against appreciated assets instead of selling, no-distribution ETF’s and ETF conversions, and tax-loss harvesting via direct indexing and tax-aware long-short strategies. This so-called tax-alpha is helping individual investors keep more in their pockets outside of the gains earned by their investments.
This year is the first full year for the additional standard deduction for older Americans, increasing the amount of income retirees can shield from federal taxes starting through 2028. The benefit is structured to apply broadly to qualifying seniors, effectively lowering taxable income on sources like Social Security, retirement account withdrawals, and investment income. For high-net-worth retirees, it creates another lever for managing taxable income—particularly in years where distributions, capital gains, or Roth conversions would otherwise push them into higher brackets.
Will AI Eat Software? by Goldman Sachs
This Goldman Sachs in-depth report considers whether generative AI will destroy the software sector. It concludes no, but there will be winners and losers. Simple, standalone tools will be commoditized if code is easier to generate, but larger platforms with users and large ecosystems that sit close to proprietary data, customer workflows, and system integration will become more important.
I’m a Financial Adviser: Silence Is Golden, But It Hurts Your Heirs More Than You Think by Kiplinger’s
Keeping your estate plan and finances too private can create confusion, delays, and unnecessary stress for heirs when decisions need to be made or assets need to be accessed. At a minimum, beneficiaries should understand the structure of your estate, where key documents are located, and who to contact, even if you choose not to share exact dollar amounts. The goal is not full financial transparency, but enough clarity and preparation to ensure your intentions are carried out efficiently and without avoidable complications.
Short-Term Oil Risk, Long-Term Market Strength by Professor Siegel
Market uncertainty has increased with rising oil and the Iran conflict, leading Professor Siegel to say that he could see a 10% correction from recent highs, but not a major market decline. The larger outlook is still positive as the economy is still growing, labor has not cracked, inflation was better than fear, and the secular AI story remains intact.
These apps are secretly stealing your data – delete them now by Tech Advisor
Popular apps are secretly harvesting user data and selling it to advertisers. Users should regularly review app permissions through iOS Privacy & Security settings or Android’s app-specific permission menus to restrict data access and delete problematic apps. As a general rule of thumb: only grant an app the permissions it actually needs for its core function. Location access should, where possible, be restricted to ‘while using the app’ and never run permanently in the background. You should only grant access to the microphone, camera and contacts when you are actively using the relevant function within the app. And for apps that request permissions that have absolutely nothing to do with their function: delete them without hesitation.
Book Recommendation
The Poet by Michael Connelly
A re-read, this is my favorite crime thriller author’s best book (IMO).
Death is reporter Jack McEvoy’s beat: his calling, his obsession. But this time, death brings McEvoy the story he never wanted to write–and the mystery he desperately needs to solve. A serial killer of unprecedented savagery and cunning is at large. His targets: homicide cops, each haunted by a murder case he couldn’t crack. The killer’s calling card: a quotation from the works of Edgar Allan Poe. His latest victim is McEvoy’s own brother. And his last…may be McEvoy himself.
Boston Corner
Boston housing market February 2026: prices, sales, and inventory by The Dorchester Post
According to Redfin, the median sale price for homes in Boston in February 2026 was about $812,500, down roughly 5 percent compared with February 2025. Homes sold more slowly than last year, with a median of 52 days on the market, and about 218 homes were sold, down from around 268 a year earlier.
The Most Affordable Top Towns in Greater Boston Right Now by Boston Magazine
Evaluating across safety, mobility, education, entertainment, housing, and more, five communities stood out for earning strong marks in nearly every category while still coming in under the million-dollar single-family median mark.
